Water insoluble azo dyestuffs



Patented Oct, 4, 1938 UNITED STATES 2,131,866 PATENT OFFICE WATER I'NSOLUBLE AZO DYESTUFFS 7 Werner Zerweck and Karl Schiitz, Frankfort-on- ,1 the-Main-Fechenheim, Germany, assignors to General Aniline Works, Inc., New York, N. Y.,

a corporation of Delaware No fDrawing.- Application March 9, 1935, Serial No. 10,326, In Germany March 17 1934 4 c1aimS'.- 101. 260-164) Our invention relates towater insoluble azodyestuffs, more particularly, those of the general formula: 1

g i f N o ONE-31 wherein Y stands for a member of the group con- 'sisting of hydrogen, methyl and halogen, and

stands for a radical of the group consisting of the n C- Y naphthalene, carbazole and benzo-carbazole series, and R1 stands for a radical of the group con-- sisting of phenyl, substituted phenyl and naphthyl, no water solubilizing group being present in the whole 'molecule. The new dyestuffs are obtained by combining in substance oron the" fiber diazo derivatives of amines which donot contain a water solubilizing group andhave the general formula:

NHa

wherein Y has the aforesaid signification' with arylamides of the benzene and naphthaleneseries 70f ortho hydroxy carboxyli'c acidsof the naphthalene, carbazole and benzo-carbazole series.

Compared. with the analogous "dyestufis ob tained by starting from diazocompounds con taining only-one aroyl group the present dyestufis are distinguished by better fastness particularly to light, boiling caustic soda solution, andironing. 1

The above bases are obtained for instance by condensing according to Friedel-Crafts" reaction nitro-aryl-dicarboxylic acid chlorides with aromatic hydrocarbons which may contain further I substituents but no group rendering the product water-soluble, and

product formed; I e V In order to further illustrate our invention the following examples are given; but we wish it, however,-to be understood that our invention is I not limited to the particular products or reaction conditions stated therein, Example-1 f 50 gi 5f wen boiled l cotton yarnis handled for about half an hourin'lliter of animpregnatreducing the condensation .i

1.5 grs. of 1-amino-2,5-dibenzoy1benzene are diazotized in the usual manner, sodium acetate and 30 grs. of sodium chloride are added and the solution thus obtained ismade up with water to 1 liter. r v

v The dyestuif thus produced on the fiber of the formula: v

ClQHN-OC- OOHa ydyes cotton scarlet shades of an excellent fastness to light, chlorine and kier-boiling.

" v Example 2 v 30 parts of 1-amino-2,4-dibenzoylbenzene are diazotized and the diazo solution thus obtained is "1 combined with an aqueous suspension of 29.3 7 parts 0f 1 (2' ,3-hydroxynaphthoylamino) 2 methoxybenzene prepared by dissolving the aforesaid quantity of the arylamide in an alcoholic caustic soda solution, diluting with water and adding acetic acid until it has a slightly alkaline reaction. The dyestuff thus obtained of the formula:

' nN ocis when dry a scarlet powder which may be used for the production of valuable scarlet color lakes.

In the following teble a number of further dyetion are described:

stufis obtainable according to the present inven- Dyestufi, obtained bfy the diazo compound 0 Combining with- Shade of the dyestufi when produced on thefiben- 1-emino-2,S-dibenzoylbenzene.

l-amino-Z, 5-dibenzoylbenzene l-amino-Z, 5-di-p-toluylbenzene 1-amino-2, 5-di-(p-chlorobenzoyl)-benzene..-

Do Do 1'amino-3, 5-dibenzoylbenzene 1-amino-2, 4-dibenzoylbenzenen l (2,3'-hydroxynaphthoylamino) 2-methoxybenzene.

l (2,3-hydroxynaphthoylamino)2, 5-dimeth0xybenzene.

1 (2,3-hydroxynaphthoylamino) 2,4-dimethoxyfi-chlorobenzene.

p-Anisidide of the 7, 8-benzocarbazole-3-hydroxy-2-cerboxy1ic acid of the formula:

1 (2', 3-hydroxynaphthoylamino) 2-ethoxybenzene.

1 (2, 3-hydroxynaphthoylamino) 2-methylbenzene.

1 (2, 3-hydroxynaphthoylamino) 2.4-dimethoxyfi-chlorobenzene.

1 (2, 3-hydroxynaphthoylamino)-naphthalene.

1 (2- hydroxycarbazole 3'- carbonylamino) 4- chlorobenzene oi the formula:

1 (2, 3-hydroxynaphthoylemino)-2-meth0xybenzene.

1 (2, 3-hydroxynaphthoylamino) 2-methyl-4- chlorobenzene.

2 (2, 3-hydroxynaphthoylamino)-naphthalene- 1 (2 hydroxycarbazole 3 carbonylamino) 4- chlorobenzene.

1 (2, 3-hydroxynaphthoylamino)-2-ethoxybenzene.

1 (2, 3-hydroxynaphthoylamino)-4-1:netl1oxybenzene.

1 (2-hydroxycarbazo1e-3-carbonylamino)-4-chlorobenzene. i

p-Anisidide 0i 7.8-benzocarbazole-3-hydroxy-2- carboxylic acid.

Terephthaloyl bis acetic acid 2 methoxy- 4'chloro-5-methylanilide oi the formula:

CO-OHPdO-NH 01 oxy-5-chlorobenzene. i V 1 (2, 3-hydroxynaphthoylamino)-naphthalene.-

Yellowish scarlet.

Scarlet.

Yellowish red.

Dark blackish violet.

Yellowish scarlet.

Yellowish red.

Alizarine like red. Chocolate like brown Scarlet.

V I Do.

Yellowish red. Chocolate like brown.

Yellowish scarlet.

Brown.

Blackish violet.

Greenish yellow.

sca rlet. 5

I Do:

Yellowish red.

r We claim: I 1. Water insolubleazo dyestufis of the general formula:

OH R w C ONH-R1 wherein Y stands for a member of the group con sisting of hydrogen, methyl and halogen, and

when produced on the fiber, cotton, valuable shades of a good fastness.

2. A water insoluble azo dyestufi of the formula:

CIGHN-O o- \N/ i r t l a which is when dry a brown powder suitable for the production of valuable brown color lakes and dyes when produced on the fiber cotton very fast chololate like brown shades.

' 3. A water insoluble azo dyestufi of the formula:

OCHa

which is when dry a scarlet powder suitable for the production of valuable scarlet color lakes and dyes when produced on the fiber cotton very fast yellowish scarlet shades.

4. A water insoluble azo dyestufi of the formula:

v 110- .QHN-OC- V 011: V

which is when dry ascarlet powder suitable for the production of valuable scarlet color lakes and dyes when produced on the fiber cotton 'very fast scarlet shades.

' WERNER ZERWECK.

KARL SCHUTZ. 

